Versatility of the cyclo-oxymercuriation route to 1,2,4-trioxanes

被引:16
作者
Bloodworth, AJ
Hagen, T
Johnson, KA
LeNoir, I
Moussy, C
机构
[1] Chemistry Department, University College London, London WC1H 0AJ
基金
英国工程与自然科学研究理事会;
关键词
D O I
10.1016/S0040-4039(96)02359-3
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The versatility of the cyclo-oxymercuriation route to 1,2,4-trioxanes is illustrated by preparing new examples with heterocyclic, unsaturated and carbohydrate substituents and by post-cyclisation modification of the substituents including oxidative cleavage of alkene and reduction, condensation and Wittig olefination of carbonyl groups. (C) 1997, Published by Elsevier Science Ltd. All rights reserved.
引用
收藏
页码:635 / 638
页数:4
相关论文
共 16 条
[1]   CHAIR CHAIR INTERCONVERSION IN SOME HIGHLY SUBSTITUTED 1,2,4-TRIOXANES AND 1,3-DIOXANES - A DYNAMIC NMR-STUDY OF A STRIKING EFFECT OF SKELETAL SUBSTITUTION [J].
ANDERSON, JE ;
BLOODWORTH, AJ ;
SHAH, A .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (10) :1927-1929
[2]   ONE-BOND C-H NMR COUPLING-CONSTANTS IN 1,2,4-TRIOXANES - A REVERSED PERLIN EFFECT [J].
ANDERSON, JE ;
BLOODWORTH, AJ ;
CAI, JQ ;
DAVIES, AG ;
TALLANT, NA .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1992, (22) :1689-1691
[3]   Structure-activity relationships of the antimalarial agent artemisinin .3. Total synthesis of (+)-13-carbaartemisinin and related tetra- and tricyclic structures [J].
Avery, MA ;
Fan, PC ;
Karle, JM ;
Bonk, JD ;
Miller, R ;
Goins, DK .
JOURNAL OF MEDICINAL CHEMISTRY, 1996, 39 (09) :1885-1897
[4]   6-HYDROXYMETHYL-1,2,4-TRIOXANES AND DERIVATIVES - AN ALTERNATIVE 1,2,4-TRIOXANE SYNTHESIS FORM BETA-GAMMA-UNSATURATED BETA-HYDROXYHYDROPEROXIDES [J].
BLOODWORTH, AJ ;
JOHNSON, KA .
TETRAHEDRON LETTERS, 1994, 35 (43) :8057-8060
[5]   SYNTHESIS OF 1,2,4-TRIOXANES VIA INTRAMOLECULAR OXYMERCURIATION [J].
BLOODWORTH, AJ ;
SHAH, A .
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1991, (14) :947-948
[6]  
BLOODWORTH AJ, 1992, J CHEM SOC CHEM COMM, P428
[7]   AN IMPROVED ROUTE TO 1,2,4-TRIOXANES USING TIN(IV) AS A HYDROGEN EQUIVALENT [J].
CAI, JQ ;
DAVIES, AG .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1992, (24) :3383-3386
[8]   1,2-3,4-DI-O-ISOPROPYLIDENE-ALPHA-D-GALACTO-HEXODIALDO-1,5-PYRANOSE AND ITS 6-ALDEYDROL [J].
HORTON, D ;
NAKADATE, M ;
TRONCHET, JM .
CARBOHYDRATE RESEARCH, 1968, 7 (01) :56-&
[9]   The deoxygenation and isomerization of artemisinin and artemether and their relevance to antimalarial action [J].
Jefford, CW ;
Vicente, MGH ;
Jacquier, Y ;
Favarger, F ;
Mareda, J ;
MillassonSchmidt, P ;
Brunner, G ;
Burger, U .
HELVETICA CHIMICA ACTA, 1996, 79 (05) :1475-1487
[10]  
KIRBY GW, UNPUB